1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol | 94683-14-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol
• 英文别名: 1,5-Diazocine-3,7-diol, octahydro-1,5-bis[(4-methylphenyl)sulfonyl]-；1,5-bis-(4-methylphenyl)sulfonyl-1,5-diazocane-3,7-diol
• CAS: 94683-14-4
• 化学式: C₂₀H₂₆N₂O₆S₂
• 分子量: 454.568
• InChiKey: BEMRKOQTVKKDDB-UHFFFAOYSA-N

物化性质

• 沸点：
  666.6±65.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol 生成 1,5-ditosyl-1,5-diazocane-3,7-dione
  参考文献：
  名称：

  Difluoramination of Heterocyclic Ketones:  Control of Microbasicity

  摘要：

  Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.

  DOI：

  10.1021/jo9718399
• 作为产物：
  描述：

  3-(p-Toluenesulfonamido)propan-2-ol 1-(p-toluenesulfonate) 在 lithium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1,5-bis-(toluene-4-sulfonyl)-[1,5]diazocane-3,7-diol
  参考文献：
  名称：

  1,3,3-三硝基氮杂环丁烷的合成

  摘要：

  用LiH处理的3-（对甲苯磺酰胺基）丙烷-2-醇-1-（对甲苯磺酸）的叔丁基二甲基甲硅烷基醚闭环成相应的氮杂环丁烷，后者容易转化为N-甲苯磺酰基-3-氮杂环丁酮肟。通过氧化氮解，后者得到1,3,3-三硝基氮杂环丁烷。

  DOI：

  10.1016/s0040-4039(00)61673-8

文献信息

• Synthesis of 1,3,3-trinitroazetidine
  作者：Theodore Axenrod、Clara Watnick、Hamid Yazdekhasti、Paritosh R. Dave

  DOI：10.1016/s0040-4039(00)61673-8

  日期：1993.10

  sulfonate) on treatment with LiH undergoes ring closure to the correponding azetidine which is readily converted to N-tosyl-3-azetidinone oxime. By oxidative nitrolysis the latter affords 1,3,3-trinitroazetidine.

  用LiH处理的3-（对甲苯磺酰胺基）丙烷-2-醇-1-（对甲苯磺酸）的叔丁基二甲基甲硅烷基醚闭环成相应的氮杂环丁烷，后者容易转化为N-甲苯磺酰基-3-氮杂环丁酮肟。通过氧化氮解，后者得到1,3,3-三硝基氮杂环丁烷。
• Facile Preparation of 3,7-Diazabicyclo[3.3.0]octane and 3,7,10-Triheterocyclic [3.3.3]Propellane Ring Systems from 1,5-Diazacyclooctane 3,7-Derivatives¹
  作者：Paritosh R. Dave、Farhad Forohar、Theodore Axenrod、Kajal K. Das、Lida Qi、Clara Watnick、Hamid Yazdekhasti

  DOI：10.1021/jo9614755

  日期：1996.1.1

  5-dinitro-3,7-diazabicyclo[3.3.0]octane, (12). Acid-catalyzed hydration of 1a, in contrast, gives the expected 5-methyl-3,7-diazabicyclo[3.3.1]nonan-1-ol (10). Reaction of the dibromide 8 with the nucleophiles, sodium sulfide, sodium oxide, and sodium p-toluenesulfonamide conveniently delivers the corresponding novel 3,7,10-triheterocyclic [3.3.3]propellanes.

  对甲苯磺酰胺和3-氯-2-（氯甲基）-1-丙烯的环二聚反应，制得N，N'-双（对甲苯磺酰基）-3,7-双（亚甲基）-1,5-二氮杂环辛烷（1a） ），并将其臭氧化为相应的3,7-二酮2a。描述了由氢化铝锂处理或1a的溴化和2a衍生的二肟的氧化偶联引发的异常环空环化。这些反应分别导致研究较少的3,7-二氮杂双环[3.3.0]辛烷环系的以下衍生物：1,5-二甲基-3,7-二氮杂双环[3.3.0]辛烷（5）， N，N'-双（对甲苯磺酰基）-1,5-双（溴甲基）-3,7-二氮杂双环[3.3.0]辛烷（8）和N，N'-双（对甲苯磺酰基）-1 ，5-二硝基-3，7-二氮杂双环[3.3.0]辛烷，（12）。相比之下，酸催化1a的水合反应可得到预期的5-甲基-3,7-二氮杂双环[3.3。1] nonan-1-ol（10）。二溴化物8与亲核试剂，硫化钠，氧化钠和对甲苯磺酰胺钠的反应可方便地产生相应的新型3,7
• 一种高稳定性的靶向接头-药物偶联物
  申请人：成都科岭源医药技术有限公司

  公开号：CN115957338A

  公开（公告）日：2023-04-14

  本发明公开了一种具有高稳定性和优异抗肿瘤效果的靶向接头‑药物偶联物，属于药物领域。本发明具体提供了一种具有特定连接子结构的药物链接组装单元，以及该药物链接组装单元与抗体连接形成的靶向接头‑药物偶联物，本发明具有特定连接子结构的靶向接头‑药物偶联物聚体含量和裸抗百分比低，DAR值合适，表现出优异的血浆稳定性、贮存稳定性和抗肿瘤作用，在制备预防和/或治疗肿瘤的药物中具有广阔的应用前景。
• Synthesis of 1,3,3-Trinitroazetidine via the Oxidative Nitrolysis of N-p-Tosyl-3-azetidinone Oxime
  作者：T. Axenrod、C. Watnick、H. Yazdekhasti、P. R. Dave

  DOI：10.1021/jo00112a014

  日期：1995.4

  The tert-butyldimethylsilyl ether of 1,3-dibromo-2-propanol reacted with p-toluenesulfonamide in the presence of K2CO3 to give the corresponding N-p-tosyl-3-azetidinol. The same azetidinol was obtained when the similarly silyl-protected 3-(p-toluenesulfonamido)propan-2-ol 1-(p-toluene-sulfonate) was treated with LiH. Desilylation and oxidation of the N-p-tosyl-3-azetidinol followed by oximation readily afforded N-p-tosyl-3-azetidinone oxime. Oxidative nitrolysis of the latter intermediate delivered 1,3,3-trinitroazetidine through a new sequence of reactions.
• Difluoramination of Heterocyclic Ketones:  Control of Microbasicity
  作者：Robert D. Chapman、Mark F. Welker、Charles B. Kreutzberger

  DOI：10.1021/jo9718399

  日期：1998.3.1

  Difluoramination of a tetrahydro-1,5-diazocine-3,7(2H, 6H)-dione to the corresponding 3,3,7,7-tetrakis(difluoramino)diazocine was achieved by a judicious choice of protecting group. Arenesulfonyl protecting groups for the diazocine nitrogens proved superior to acetyl during the slow disruption of the transannular bridge in 9-oxa-3,7-diazabicyclo[3.3.1]nonane intermediates by difluorosulfamic acid, While a 1,5-ditosyl derivative failed to proceed beyond the product of addition of difluoramine to one ketone carbonyl (hemiaminal 6), the use of 4-nitrobenzenesulfonyl as the protecting groups lowered the nitrogens' basicities below that of the oxygen site in the dione and intermediates, allowing the reaction to proceed to a gem-bis(difluoramino)diazocine product (11). A safer procedure for handling difluoramine is described.